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CAS No. : | 185017-72-5 | MDL No. : | MFCD03095218 |
Formula : | C6H5BrClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JVDQYSIJBRTRMS-UHFFFAOYSA-N |
M.W : | 206.47 | Pubchem ID : | 2734418 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.91 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.5 cm/s |
Log Po/w (iLOGP) : | 2.16 |
Log Po/w (XLOGP3) : | 2.9 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 3.14 |
Consensus Log Po/w : | 2.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.0749 mg/ml ; 0.000363 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.83 |
Solubility : | 0.305 mg/ml ; 0.00147 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.89 |
Solubility : | 0.0268 mg/ml ; 0.00013 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.57 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; water; at 20℃; for 72h; | Example 633-[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-6-methyl-2-pyridinecarboxylic acidCla)2-Chloro-5-(2-chloro-6-methyl-3-pyridinyl)-JV-(tricyclo[3.3.1.13'7]dec-l-ylmethyl)-benzamideA mixture of [4-chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid (Example 2 (a)) (174 mg), <strong>[185017-72-5]3-bromo-2-chloro-6-methyl-pyridine</strong> (104 mg),potassium carbonate (138 mg) and Z?w(triphenylphosphine)palladium(II) chloride (27 mg)in tetrahydrofuran (2 mL) and water (2 mL) was stirred at room temperature under anitrogen atmosphere over 72 hours. The mixture was filtered through diatomaceous earth,washing with methanol, and the filtrate was concentrated in vacuo. Purification bychromatography (SiOa, zsohexane:emyl acetate 1:1 as eluant) gave the sub-title compoundas a solid (135 mg).MS: APCI(+ve) 429/431 (M+H*) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In acetonitrile; at 120 - 170℃; for 2h;Microwave irradiation; | Example 52; (RS)-1-Benzenesulfonyl-4-[4-(3-bromo-6-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-cyclohexyl-imidazolidin-2-oneStep 1: A solution of <strong>[185017-72-5]3-bromo-2-chloro-6-picoline</strong> (0.2 g), piperazine (0.083 g) and triethylamine (0.096 g) in acetonitrile (5 ml) was heated in the microwave apparatus: 30 min at 120 C. followed by 60 min at 150 C. and 30 min at 170 C. The mixture was concentrated and the product was purified by chromatography (SiO2, CH2Cl2=>CH2Cl2/CH3OH 4:1) to give 1-(3-bromo-6-methyl-pyridin-2-yl)-piperazine (0.05 g) as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; 3-chloro-benzenecarboperoxoic acid; In methanol; chloroform; ethyl acetate; | (5-Bromo-6-methoxy-pyridin-2-yl)-methanol (356a) step a-To a solution of <strong>[185017-72-5]3-bromo-2-chloro-6-methyl-pyridine</strong> (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50 C. overnight. The resulted solution was cooled and partitioned between DCM and sat'd. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of <strong>[185017-72-5]3-bromo-2-chloro-6-methyl-pyridine</strong> 1-oxide (357a) as a white solid. step b-A solution of 357a (0.5 g) and 0.5 M NaOMe/MeOH (4.9 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue loaded on a SiO2 column and eluted with 5% MeOH/DCM to afford 3-bromo-2-methoxy-6-methyl-pyridine 1-oxide (357b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol; for 168h;Reflux; | Example 3: Lambda/-[1 -(4-Chlorophenyl)cyclopropyl]methyl}-6-methoxy-5-(4-methyl-1 H- imidazol-1 -yl)pyridine-2-carboxamide (3)Step 1 . Synthesis of 3-bromo-2-methoxy-6-methylpyridine (C14). A mixture of <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (75.4 g, 0.365 mol) and sodium methoxide (59.1 g, 1 .1 mol) in absolute methanol (700 mL) was heated at reflux for 5 days. Additional sodium methoxide (1 equivalent) was added, and the mixture was heated at reflux for 2 days. The solvent was removed under reduced pressure, and the residue was partitioned between water and dichloromethane. The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated to provide the title product. Yield: 70.3 g, 0.348 mol, 95%. |
46% | In tetrahydrofuran; at 0 - 100℃; | To a cooled (0 C) solution of <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (300 mg, 1.45 mmol) in tetrahydrofuran (20 mL), add sodium methoxide (1.57 g, 29 mmol), slowly with stirring. Allow the mixture to warm to ambient temperature and stir overnight. Add additional sodium methoxide (500 mg) and stir at 100 C overnight. Quench with water (20 mL), extract three times with ethyl acetate (30 mL). Combine the organics and wash with water then brine, and dry over sodium sulphate. Filter and concentrate to give the title product as a yellow solid (135 mg, 46%). 1HNMR (MeOH-d4): delta 7.72(d, 1H), 6.70(d, 1H), 3.93(s, 3H), 2.38(s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | a) l-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 min. Stirring was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL). The combined extracts were washed with ice water (50 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 min.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): m/e = 198.1 [MH+] | |
70% | a) 1-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 mm. Stuffing was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL).The combined extracts were washed with ice water (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 mm.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): mle = 198.1 [MHi. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90℃; for 1h; | In 21 mL of carbon tetrachloride, <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90C for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol = 100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); caesium carbonate; In toluene; at 100℃; for 3h;Inert atmosphere; | To a vial containing 3-(3,5-dimethylisoxazol-4-yl)aniline (96 mg, 0.5 10 mmol)was added <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (211 mg, 1.02 mmol), cesium carbonate(332 mg, 1.02 mmol), chloro(2-dicyclohexylphosphino-2 ? ,4 ? ,6? -triisopropyl- 1,1? - biphenyl)[2-(2? -amino-i, 1? -biphenyl)jpalladium(II) (CAS 1310584-14-5, 10.0 mg, 0.013 mmol), and toluene (2 mL). The resulting suspension was degassed by bubbling argon through the reaction mixture. The vial was capped with a pressure-safe septum cap andheated to 100 C for 3 h. The reaction mixture was cooled to room temperature and filtered through a pad of silica gel. The filter pad was washed with ethyl acetate. The filtrate was concentrated and purified by silica gel chromatography with 0 - 100% ethyl acetate in hexanes. The product containing fractions were evaporated to give 2-chloro-N- (3 -(3 ,5-dimethylisoxazol-4-yl)phenyl)-6-methylpyridin-3 -amine (49 mg, 31%) as a palebrown solid: HPLC: RT=0.97 mm (Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0.05%TFA, 1 mm gradient, wavelength=254nrn); MS (ES): m/z= 314.2/3 15.9 35C1/37C1 [M+ljt |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); caesium carbonate; In toluene; at 100℃; for 5h;Inert atmosphere; | To a vial containing 3-amino-S -(3,5 -dimethylisoxazol-4-yl)benzonitrile (80 mg,0.375 mmol) was added toluene (2 mL), <strong>[185017-72-5]3-bromo-2-chloro-6-methylpyridine</strong> (85 mg,0.413 mmol), cesium carbonate (244 mg, 0.750 mmol) and chloro(2-dicyclohexylphosphino-2? ,4? ,6 ? -triisopropyl- 1,1? -biphenyl) [2-(2? -amino- 1,1? -biphenyl)jpalladium(II) (CAS1310584-14-5, 7.4 mg, 9.38 imol). The reaction mixture was degassed by bubbling argon through the reaction mixture. The vial was capped with a pressure safe septum screw-cap and heated at 100 C. After 5 h, the reaction mixture was cooled, diluted with dichloromethane, and filtered through celite. The filtrate was concentrated and purified by silica gel chromatography to give 3-((2-chloro-6-methylpyridin-3-yl)amino)-5 -(3,5 -dimethylisoxazol-4-yl)benzonitrile (29 mg, 23%):HPLC: RT=0.93 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.05%TFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z 339.1/340.9 35C1/37C1 [M+ljt |
Tags: 185017-72-5 synthesis path| 185017-72-5 SDS| 185017-72-5 COA| 185017-72-5 purity| 185017-72-5 application| 185017-72-5 NMR| 185017-72-5 COA| 185017-72-5 structure
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H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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